Journal
TETRAHEDRON LETTERS
Volume 54, Issue 16, Pages 2097-2100Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.02.023
Keywords
Organocatalysis; Monofluorination; Hypervalent iodine; Alkynylation; Phenylsulfonyl derivatives
Categories
Funding
- Ministry of Education of the Czech Republic [MSM0021620857]
- Czech Science Foundation [P207/10/0428]
- Education for Competitiveness Operational Programme (ECOP)
- European Social Fund
- state budget of the Czech Republic
- [CZ.1.07/2.3.00/30.0022]
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Organocatalytic alkynylation of nucleophilic fluorocarbons using hypervalent iodine compounds under cinchona-based catalysis, namely using O-allyl N-anthracenyl cinchona alkaloid derivative II, is described. The reaction gives the final fluoro-propargyl compounds in good to excellent yields (up to 91%) and with moderate to low enantioselectivity (up to 61% ee). The reaction represents the first example of the use of hypervalent iodine compounds for the construction of fluorinated compounds and opens access to the preparation of biologically attractive compounds such as 1,2,3-triazoles. (c) 2013 Elsevier Ltd. All rights reserved.
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